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$290+ Cheap flights from Aspen (ASE) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — MDW
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheap flight deals from Aspen to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated abril 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$419
(Delta)

One-way from

$290
(Delta)

Popular in

March

Cheapest in

September

Average price

$439
Provider with most accurate pricing for Aspen Pitkin County-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Aspen Pitkin County-Chicago Midway flights.
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From Aspen Pitkin County to Chicago Midway
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One-way flight from Aspen Pitkin County to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Aspen to Midway

Cheapest flights from Aspen to Midway
Explore the most affordable flight options available from Aspen to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 29, 2025.

This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/278:05 amASE - MDW
1 stop8h 57mDelta
dom. 6/296:00 amMDW - ASE
1 stop6h 22mDelta
Deal found 4/28$419

Cheapflights Fare Finder

Customize your flight search to find flights from Aspen to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 29, 2025.
Use the filters below to find and compare flights from Aspen to Chicago Midway Airport that are best for you.

Fly from

Aspen

Fly to

Midway

Route

Depart

Return

Price

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

vie. 6/27

8:05 am-6:02 pm

1 stop8h 57m

Chicago Midway

dom. 6/29

6:00 am-11:22 am

1 stop6h 22m

$419

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

vie. 6/13

8:05 am-3:41 pm

1 stop6h 36m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

  • Most accurate provider: When it comes to deals on Aspen-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Aspen-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Aspen-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Aspen-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Aspen-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Aspen to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Aspen with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Aspen to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated abril 29, 2025.
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,936 reviews
Delta
8.0
Very good
7,936 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Aspen to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Aspen to Chicago Midway?

    Located just 3.5 mi from the city center, Aspen Pitkin County is the airport most travelers will use when flying to Chicago Midway from Aspen. Booking flights from Pitkin County (ASE) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • Can I find deals for flights from Aspen to Midway that include hotel bookings?

    Yes. In addition to deals on Aspen to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aspen to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aspen to Midway.

  • Can I find deals for business class flights from Aspen to Midway?

    Yes. Cheapflights offers flight deals from Aspen to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Aspen to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Aspen to Chicago Midway Airport (average of $160). Flying from Aspen to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Aspen?

Book flights to Aspen if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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